Patent GB-664779-A (GB)
Title: Improvements relating to the production of organic phosphate esters
IPC: B03D1/014
Filed: 1949-05-09
Abstract: Phosphate esters of the general formula <FORM:0664779/IV (b)/1> wherein X1 and X2 represent sulphur or oxygen, R represents hydrogen or an alkyl radical, R1 and R2 are identical or different and represent alkyl (saturated or unsaturated, straight or branched chain or cyclic), aralkyl or aryl radicals, which may carry nitro or halogen substituents (e.g. methyl, ethyl, n-propyl, isopropyl, isobutyl, sec.-amyl, n-hexyl, 2-ethylhexyl, n-octyl, n-decyl, n-dodecyl, oleyl, cetyl, ceryl, allyl, bromomethyl, 2-chloroethyl, cyclohexyl, benzyl, phenyl, p-chlorophenyl or o-, m- or p-nitrophenyl), R3 and R4 represent hydrogen or alkyl or aryl radicals and m is an integer not exceeding 5, are manufactured by reacting a haloacylurea of the general formula <FORM:0664779/IV (b)/2> (wherein Z represents chlorine or bromine) with an alkali or alkaline-earth metal or ammonium salt of an acid phosphate of the general formula <FORM:0664779/IV (b)/3> or with the free acid phosphate in the presence of a basic alkali or alkaline-earth metal or ammonium compound having sufficient alkalinity to neutralize the acid phosphate (e.g. sodium, potassium, barium, magnesium or lithium carbonate, sodium, potassium, calcium, strontium or magnesium hydroxide, sodium hydrosulphide or borate, sodium, potassium or magnesium pyrophosphate, tripotassium arsenate or arsenite, or barium or disodium phosphate).  The reaction is preferably carried out at 20-150 DEG  C. in the presence of a solvent (e.g. lower aliphatic monohydric alcohols, ketones, aliphatic esters, saturated aliphatic nitriles, dioxane, nitrobenzene, chlorobenzene, toluene, xylene, chloroform, carbon tetrachloride, 1 : 2-dimethoxyethane or trialkyl phosphates).  The products are useful as pesticides, corrosion inhibitors, plasticizers, flotation agents and petroleum additives. Examples describe the preparation of 0 : 0-diethyl, -dimethyl, -di-n-amyl and -diphenyl mercaptoacetylurea dithiophosphate, 0 : 0-diethyl a  - mercaptoisovalerylurea dithiophosphate, 0 : 0 - di - isopropyl 1 - mercaptoacetyl-3-methylurea dithiophosphate, 0 : 0-di-n-decyl 1 - mercaptoacetyl - 3 - phenylurea dithiophosphate, 0 : 0-diethyl mercaptoacetylurea monothiophosphate and diethyl glycollylurea phosphate.ALSO:Additives to petroleum oils comprise organic phosphate esters of the general formula <FORM:0664779/III/1> wherein X1 and X2 represent sulphur or oxygen.  R represents hydrogen or an alkyl radical, R1 and R2 are identical or different and represent alkyl (saturated or unsaturated, straight or branched chain or cyclic), aralkyl or aryl radicals, which may carry nitro or halogen substituents (e.g. methyl, ethyl, n- or isopropyl, isobutyl, sec.-amyl, n-hexyl, 2-ethylhexyl, n-octyl, n-decyl, n-dodecyl, oleyl, cetyl, ceryl, allyl, bromomethyl, 2-chlorethyl, cyclohexyl, benzyl, phenyl, p-chlorophenyl or o-, m- or p-nitrophenyl), R3 and R4 represent hydrogen or alkyl or aryl radicals, and m is an integer not exceeding 5.ALSO:As flotation reagents may be employed organic phosphate esters of the general formula <FORM:0664779/II/1> wherein x1 and x2 represent sulphur or oxygen, R represents hydrogen or an alkyl radical, R1 and R2 are identical or different and represent alkyl (saturated or unsaturated, straight or branched chain or cyclic), aralkyl or aryl radicals, which may carry nitro or halogen substituents, e.g. methyl, ethyl, n- or iso-propyl, isobutyl, sec.-amyl, n-hexyl, 2-ethylhexyl, n-octyl, n-decyl, n-dodecyl, oleyl, cetyl, ceryl, alkyl, bromomethyl, 2-chloroethyl, cyclohexyl, benzyl, phenyl, p-chlorophenyl or o-, m- or p-nitroR3 and R4 represent hydrogen or alkyl or aryl radicals, and m is an integer not exceeding 5.